The chiral recognition abilities of the two selectors are opposite . Since our excess is very low, our substance was nowhere near being pure. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity You'll get a detailed solution from a subject matter expert that helps you learn core concepts. As a diprotic acid, succinic acid undergoes two successive deprotonation reactions: The pKa of these processes are 4.3 and 5.6, respectively. Neutral phenylsuccinic acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. [12] Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate. 2. the phenylsuccinic acid will precipitate and can be filtered out while the proline is very soluble in water HCl can also be added to (-)-phenylsuccinic acid to release it from any salt which may have formed specific rotation = alpha (observed rotation in degrees)/ l (dm)*c (g/ml) optical purity aka = enantiomeric excess 7, 4 (2007). The site owner may have set restrictions that prevent you from accessing the site. For Research Use Only. Moreover, the cold water wash and filtration performed was able to recover the crude solid. Proceed to measure the specific rotation of the sample and calculate the enantiomeric excess 4) Recrystallization: The recovered acid contains contaminants- possibly some left-over proline and some HCl or some of the enantiomeric succinic acid. Resolved (S)-acid: 0, Theoretical yield: 1 2 =0 configuration enantiomer, the other diastereomer must be more soluble during the filtration Enantiomers are distinguished from cach other by designations like "R" or "S", "D" or "L", or by the direction of the rotation they cause ("+" or "-") Since the presence of optical activity is an indication of a particular configuration of atoms, any change in optical activity that occurs during a chemical reaction offers a way to study the kind of configurational change that accompanies the reaction. [37] The oncogenic mechanism caused by mutated SHD is thought to relate to succinate's ability to inhibit 2-oxogluterate-dependent dioxygenases. this experiment, a reflux reaction [citation needed], As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Through these mechanisms, succinate accumulation has been shown to regulate production of inflammatory cytokines. A. V. Trask, N. Shan, W. D. S. Motherwell, et al., Chem. Question: In this experiment, racemic (RS)-phenylsuccinic acid is separated (resolved) into optically active cautiouets in a sequence of two steps. The phenylsuccinic acid gave up two positives, so it is a dianion. Sorry, it seems JavaScript is not enabled in your browser. M. J. Zaworotko, Cryst. For Research Use Only. Since PHDs have an absolute requirement for molecular oxygen, this process is suppressed in hypoxia allowing HIF1 to escape destruction. An ideal solvent would completely precipitate one diastereomer while the other coe remained in the solution. RST is the consecutive number of the substance in the series ABC. Nonsuperposable mirror image molecules are called enantiomers. 3) Recovery of resolved acid: Add all of the solid to 8 mL of ice-cold 6 M HCl in a small beaker or glass tube, place the sample in an ice bath. Note that the two diastercomeric salts (S.S) and (R.S) differ in their mions (phenylsuccinate), which are nonsuper-posable mirror images, but have identical cations (L-proline). The calculated specific rotation came out to be 60.65, meaning that it was not optimally pure but the fact that it was positive meaning that it was more of an S enan-tiomer than an R which was preferred. [citation needed], Succinate is a key intermediate in the tricarboxylic acid cycle, a primary metabolic pathway used to produce chemical energy in the presence of O2. acid is partially soluble in water, so HCl was used as a strong acid to protonate the anion. The glyoxylate cycle is utilized by many bacteria, plants and fungi and allows these organisms to subsist on acetate or acetyl CoA yielding compounds. Most often, these pieces can attach to the enzyme only in one particular orientation. Structure, properties, spectra, suppliers and links for: (+)-Phenylsuccinic acid, 4036-30-. High concentrations of succinate will mimic the hypoxia state by suppressing PHDs,[37] therefore stabilizing HIF1 and inducing the transcription of HIF1-dependent genes even under normal oxygen conditions. [30] In the second step of mitochondrial export, succinate readily crosses the outer mitochondrial membrane through porins, nonspecific protein channels that facilitate the diffusion of molecules less than 1.5 kDa. In animal models, pharmacological inhibition of ischemic succinate accumulation ameliorated ischemia-reperfusion injury. [37][41] Loss-of-function mutations in the genes encoding succinate dehydrogenase, frequently found in hereditary paraganglioma and pheochromocytoma, cause pathological increase in succinate. X`I%&/m{JJt`$@iG#)*eVe]f@{{;N'?\fdlJ!?~|? First, we exploit its chemical nature it is m acid) by treating it with an optically active biologically produced base, L-proline. Immediately retum the contents to the boiling flask and swirl. J. M. Chen, Z. succinic acid and proline to pro- Rep. 64, 10381042 (2019). Optical Rotation: []=obscl[]=(0.03992/m)( 1 )=60 Growth Des. A suitable solvent is found by trial and error. Collect the purified crystals by vacuum filtration and rinse with 10mL of ice cold water. [5], As a radical group it is called a succinyl (/sksnl/) group. 5 mL of DI water. [6][38], Metabolic signaling involving succinate can be involved in inflammation via stabilization of HIF1-alpha or GPR91 signaling in innate immune cells. . Consider a racemic chical compound (a sample in which there are exactly equal populations of both enantiomers). HIF1 is known to induce transcription of more than 60 genes, including genes involved in vascularization and angiogenesis, energy metabolism, cell survival, and tumor invasion. Diastecomers are not chemically identical, and so they differ in common physical properties. Pharmacol. Inhalation: [12], In 2004, succinate was placed on the US Department of Energy's list of top 12 platform chemicals from biomass. with another chiral molecule. acid into separable diastereomers. Growth Des. Copyright 2007-2023 Santa Cruz Biotechnology, Inc. All Rights Reserved. However, if the acid is combined with an optically active base, such as (-)-proline, the diastereomers which form have different _____ in isopropyl alcohol. InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14)/t8-/m0/s1, CSID:643286, http://www.chemspider.com/Chemical-Structure.643286.html (accessed 08:22, Mar 4, 2023), Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agencys EPISuite, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. Orgo exam notes - Exam noted for organic chemistry. Single crystal structures, thermal analysis, powder X-ray analysis and equilibrium solubility in water and ethanol of the cocrystals were measured. Percent recovery: 00 100 =4% [30] In general, leakage from the mitochondria requires succinate overproduction or underconsumption and occurs due to reduced, reverse or completely absent activity of SDH or alternative changes in metabolic state. The resulting solid acid can be recovered by filtration. Expert Answer. is a proton donor making proline The information below may provide an Experiment 4: Resolution of Phenylsuccini, The purpose of this experiment is to be able to convert enantiomers of phenylsuccini, ing the enantiomer by neutralizing the salt created to find the optical purity by measuring the op-, The Methodology of the Social Sciences (Max Weber), Campbell Biology (Jane B. Reece; Lisa A. Urry; Michael L. Cain; Steven A. Wasserman; Peter V. Minorsky), Chemistry: The Central Science (Theodore E. Brown; H. Eugene H LeMay; Bruce E. Bursten; Catherine Murphy; Patrick Woodward), Psychology (David G. Myers; C. Nathan DeWall), Principles of Environmental Science (William P. Cunningham; Mary Ann Cunningham), Educational Research: Competencies for Analysis and Applications (Gay L. R.; Mills Geoffrey E.; Airasian Peter W.), Give Me Liberty! The solid was recrystallized and the final solid is filtered out. Molecular Formula:C10H10O4 Molecular Weight:194.19 Section 10 - Stability and Reactivity Chemical Stability:Stable under normal temperatures and pressures. 8, 4533 (2008). 48, 5009 (2006). The difference, however, is subtle Pure samples of mirror image molecules behave identically toward physical tests like melting and boiling points and solubility in given solvents The only way that these isomers differ physically is the direction in which they rotate plane-polarized light -their optical activity. Sample will be analyzed by polarimetry. [9], Like most simple mono- and dicarboxylic acids, it is not harmful but can be an irritant to skin and eyes. [35] Simultaneous to substrate oxidation, they convert 2-oxoglutarate, also known as alpha-ketoglutarate, into succinate and CO2. [30], SUCNR1 is highly expressed on immature dendritic cells, where succinate binding stimulates chemotaxis. : an American History (Eric Foner), Forecasting, Time Series, and Regression (Richard T. O'Connell; Anne B. Koehler), Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. To purify, recrystallize the (S)-phenylsuccinic acid precipitate from water. volumes of cold water. MONOCLONAL MOUSE ANTI-RABBIT/GOAT SECONDARY ANTIBODIES, POLYCLONAL GOAT/RABBIT ANTI-MOUSE SECONDARY ANTIBODIES, ISOTYPE SPECIFIC MOUSE IgG BINDING PROTEINS, PROTEIN A, G-PLUS & L AGAROSE IP REAGENTS, NUCLEOTIDES, PEPTIDES, PROTEINS & AMINO ACIDS, AUTORADIOGRAPHY FILM, TAPE AND PLASTIC WRAP. In living organisms, primarily succinate, not succinic acid, is found. At the end of 30 minutes, turn off and remove the heating mantle. Most often, these pieces can attach to the enzyme only in one particular, orientation. C. C. Seaton, CrystEngComm 13, 6583 (2011). May cause respiratory tract irritation. Solubility: Not available. Succinate exits the mitochondrial matrix and passes through the inner mitochondrial membrane via dicarboxylate transporters, primarily SLC25A10, a succinate-fumarate/malate transporter. ADS [41], Succinate accumulation under hypoxic conditions has been implicated in the reperfusion injury through increased ROS production. C. B. Aakery and D. J. Salmon, CrystEngComm 7, 439 (2005). comes insoluble in water. [28], Succinate serves as a modulator of blood pressure by stimulating renin release in macula densa and juxtaglomerular apparatus cells via GPR91. These chemicals are invariably synthesized by catalysts called I enzymes, which are large chiral molecules specially designed to carry out a particular chemical transformation. In humans, three HIF prolyl 4-hydroxylases regulate the stability of HIFs. [5], Historically, succinic acid was obtained from amber by distillation and has thus been known as spirit of amber. Thus, succinate is thought to play a role in liver homeostasis. The acid and base are structurally more complex than HCl and NH3, but the concept is the same. Commun. L. D. Liu, S. L. Liu, Z. X. Liu, and G. G. Hou, J. Mol. so they can be created by reacting bvseo-msg: The resource to the URL or file is currently unavailable.. Optically active reagents have long been important in studies of reaction mechanisms because they may offer glimpses at the molecular details of the process as the reaction proceeds. The recovered solid is the less-soluble diastereomeric salt of the pair that you made. Share Improve this answer Follow edited Oct 28, 2019 at 15:24 5.03E-005 mm Hg (25 deg C, Mod-Grain method) Water Solubility Estimate from Log Kow (WSKOW v1.41): Water Solubility at 25 deg C (mg/L): 4.234e+004 log Kow . [7][32] Succinate may enhance adaptive immunity by triggering the activity of antigen-presenting cells that, in turn, activate T-cells. This enzyme complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone via the intermediate electron carriers FAD and three 2Fe-2S clusters. Eng. process so the S configuration enantiomer will precipitate into the flask, leaving the R enan- To begin, dissolve 1.94g of racemic phenylsuccinic acid into 50mL of isopropanol in a 100mL round bottom flask. Crystallogr. stream 2-oxoglutarate-dependent dioxygenases bind substrates in a sequential, ordered manner. The solid that results is now-resolved phenylsuccinic acid in its protonated form. phenylsuccinic acid would bind to the proton (H+), where it loses its negative charge and be- phenylsuccinic acid (H 2A) as the model enantiomers. Specific rotation is defined as [.." - r/le where "-the specific rotation (at 200C using the "D line" of a sodium lamp: units arc (deg x ml. Let Cool for 15 min: very chunky, wet-sand-like consistency, almost solid - slushy, ter. Not Intended for Diagnostic or Therapeutic Use. By signing up, you indicate that you have read and agree to the terms in our privacy policy. tical while diastereomers are not Pull air through the solid for a couple of minutes after the last wash to evaporate most of the acetone. PubMedGoogle Scholar. [26] As such, succinate links TCA cycle dysfunction or metabolic changes to cell-cell communication and to oxidative stress-related responses. %PDF-1.4 Give the % of each enantiomer. 4,4-Bipyridine and 1,2-bis(4-pyridyl)ethane were combined with achiral, racemic mixture or pure enantiomers of selected carboxylic acids with similar constituents (p-toluic acid, rac-2-phenylbutyric acid, racemic or S-phenylsuccinic acid). 1 0 obj duce salt. CH 105 Exp 1 Aspirin_with IR Spectrum.pdf, The opioid in New Hamsphire (Autosaved).docx, Muscle There are three types of muscle tissues cardiac muscles which are found, 20 Run other transforms on other websites Task 4 SpiderFoot Independent 17, Malicious unauthorized penetration into information systems Fraud Using, Mathematics_of_finance_Solutions_to_revi.pdf, Part D Calculate the bond dissociation energy needed to break all the bonds in a, Lower environmental costs If firms improve the efficiency of their energy usage, The operations manager schedules quarterly reviews of office equipment whether, Analysis of the Human Relations Theory of Management.docx, Stats Medic - AP Stats - Rules for Means and Variances.pdf, Philippi coins with HPAK countermark 103 Burnet et alii 1992 22 287 Touratsoglou, Uniform Trade Secrets Act I trade secret law developed under the common law but, _Antigone, Scenes 3-5_ Integrated Language Skills.docx, First however it explicates the nature of accounting theories determines the. In this study, we investigated CCN activity of inorganic salt (sodium chloride and ammonium sulfate) and dicarboxylic acid (including malonic acid (MA), phenylmalonic acid (PhMA), succinic acid (SA), phenylsuccinic acid (PhSA . stacking interaction leads to the formation of 3D supramolecular structure. vacuum filter the reaction mixture & wash salt with 2 15mL of acetone. Who are the experts? [10] 1,4-Butanediol (BDO) can be synthesized using succinic acid as a precursor. Cross), Civilization and its Discontents (Sigmund Freud), Biological Science (Freeman Scott; Quillin Kim; Allison Lizabeth), Brunner and Suddarth's Textbook of Medical-Surgical Nursing (Janice L. Hinkle; Kerry H. Cheever). https://doi.org/10.1134/S1063774519070125. This is an ordinary acid-basc reaction that produces a salt. [29] As of 2016 the inhibition of succinate-mediated ROS production was under investigation as a therapeutic drug target.[29]. Exact concentration: 0 10 mL=0. RET at mitochondrial respiratory complex 1, the complex normally preceding SDH in the electron transport chain, leads to ROS production and creates a pro-oxidant microenvironment.[29]. of this substance have not been fully investigated. Alternate Names: Phenylsuccinic acid. N. Shan, F. Toda, and W. Jones, Chem. [30] Stimulation of GPR91 triggers at least two signaling pathways in the heart: a MEK1/2 and ERK1/2 pathway that activates hypertrophic gene expression and a phospholipase C pathway which changes the pattern of Ca2+ uptake and distribution and triggers CaM-dependent hypertrophic gene activation. This process produced two diastereomers where the more soluble compound was removed by the HCl. In this experiment, a reflux reaction is conducted between the pheny-succinic acid and proline to produce salt. Scratch inside this test tube several minutes until the contents begin to get cloudy. . Write a review Ask a question. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. Pure samples of mirror image molecules. Skin: The interactive pathway map can be edited at WikiPathways: Learn how and when to remove this template message, JmjC domain-containing histone lysine demethylase, Institute for Occupational Safety and Health, "Product Information Sheet: Succinic Acid", "Succinate, an intermediate in metabolism, signal transduction, ROS, hypoxia, and tumorigenesis", "Ischaemic accumulation of succinate controls reperfusion injury through mitochondrial ROS", Ullmann's Encyclopedia of Industrial Chemistry, "NNFCC Renewable Chemicals Factsheet: Succinic Acid", "Succinate production in Escherichia coli", "Industrial Systems Biology of Saccharomyces cerevisiae Enables Novel Succinic Acid Cell Factory", "Top Value Added Chemicals from Biomass, Volume 1: Results of Screening for Potential Candidates from Sugars and Synthesis Gas", "1,4-Butanediol (BDO) Market Analysis By Application (Tetrahydrofuran, Polybutylene Teraphthalate, Gamma-Butyrolactone & Polyurethanes), And Segment Forecasts To 2020", "Design and Applications of Biodegradable Polyester Tissue Scaffolds Based on Endogenous Monomers Found in Human Metabolism", "Succinic acid in the FDA SCOGS Database", "Overview of pharmaceutical excipients used in tablets and capsules", "Differential effects of complex II on mitochondrial ROS production and their relation to cardioprotective pre- and postconditioning", "Improved Succinate Production by Metabolic Engineering", "Intermediates of Metabolism: From Bystanders to Signalling Molecules", "The succinate receptor as a novel therapeutic target for oxidative and metabolic stress-related conditions", "Succinate metabolism: a new therapeutic target for myocardial reperfusion injury", "GPR91: expanding the frontiers of Krebs cycle intermediates", "Insight into SUCNR1 (GPR91) structure and function", "Inhibition of -KG-dependent histone and DNA demethylases by fumarate and succinate that are accumulated in mutations of FH and SDH tumor suppressors", "Oncometabolites: linking altered metabolism with cancer", "Inhibition of hypoxia-inducible factor (HIF) hydroxylases by citric acid cycle intermediates: possible links between cell metabolism and stabilization of HIF", "Succinate is a danger signal that induces IL-1 via HIF-1", "Metabolic reprogramming in macrophages and dendritic cells in innate immunity", "Oncometabolites: Unconventional triggers of oncogenic signalling cascades", "Succinate dehydrogenase and fumarate hydratase: linking mitochondrial dysfunction and cancer", Flame Retardant Finishing of Cotton Fleece Fabric: Part IV-Bifunctional Carboxylic Acids, Calculator: Water and solute activities in aqueous succinic acid, ScienceDirect: Succinic Acid - Production of organic acids and enzymes / biocatalysts from food waste, PubChem: Compound Summary for Succinic Acid, https://en.wikipedia.org/w/index.php?title=Succinic_acid&oldid=1135423431, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Short description is different from Wikidata, Articles with unsourced statements from January 2021, Articles lacking reliable references from March 2017, Creative Commons Attribution-ShareAlike License 3.0, This page was last edited on 24 January 2023, at 15:55. Less The diastereomeric salt formed between the (+)-phenylsuccinic acid and (-)-proline is much ___ soluble in isopropyl alcohol than the diastereomeric salt formed between the . Correspondence to ACD/Labs Percepta Platform - PhysChem Module, US Environmental Protection Agencys EPISuite, Compounds with the same molecular formula, Search Google for structures with same skeleton, CAUTION: May irritate eyes, skin, and respiratory tract. Solubility:Not available. The toxicological D. K. Bucar, R. F. Henry, X. C. Lou, et al., Mol. Accumulation of either fumarate or succinate reduces the activity of 2-oxoglutarate-dependent dioxygenases, including histone and DNA demethylases, prolyl hydroxylases and collagen prolyl-4-hydroxylases, through competitive inhibition. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA). OPTICAL RESOLUTION OF 2-PHENYLSUCCINIC ACID (From R. Stephani and V. Cesare, Journal of Chemical Education 74, 1226, 1997) 1) Background: The purposes of this experiment are to show how enantiomers can be separated if they are converted into a mixture of diastereomers and to understand how careful choice of solvent can permit selective precipitation of one compound from a mixture of compounds. 1).Factors affecting the extraction efficiency were investigated, namely the influence of the types of organic solvents and -CD derivatives, iso-butyl tartrate . /Producer(Sub Systems, Inc.)/CreationDate(D:20211226231644+05'00')/ModDate(D:20211226231644+05'00')/Creator(Sub Systems, Inc.) Purpose: Este site coleta cookies para oferecer uma melhor experincia ao usurio. ), . The experiments were carried out in a traditional SS apparatus but with collaborative chiral selectors: dibenzoyl-L-tartaric acid (L-DBTA) in the organic phase and hydroxypropyl--cyclodextrin (HP--CD) in the aqueous phase. 100mL round bottom flask. [10] Global production is estimated at 16,000 to 30,000 tons a year, with an annual growth rate of 10%. Not Intended for Diagnostic or Therapeutic Use. Chirality is a necessary condition for the existence of optical activity (the ability to cause rotation of the plane of polarized light). 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. This new feature enables different reading modes for our document viewer.By default we've enabled the "Distraction-Free" mode, but you can change it back to "Regular", using this dropdown. N. Shan, A. D. Bond, and W. Jones, Cryst. [30] The G-protein coupled receptor, GPR91 also known as SUCNR1, serves as the detector of extracellular succinate. please email the information below to [emailprotected]. ;DgEvzv {M aK. RECEIVE -15-CRUZ CREDITS. In the liver, succinate serves as a paracrine signal, released by anoxic hepatocytes, and targets stellate cells via GPR91. & Azadbakht, A. Co-Crystal of Phenylsuccinic Acid and 4,4'-Bipyridine: Synthesis, Characterization, Crystal Structure, and Supramolecular Interactions. [8][29] During ischemia, succinate accumulates. Provided by the Springer Nature SharedIt content-sharing initiative, Over 10 million scientific documents at your fingertips, Not logged in Added to cooled 10 mL 6 HCl: Reaction immediately but not cloudy enough They are potentially separable by ordinary physical methods like different solubility in a given solvent, which allows recovery of a single diastereomer Subsequently, the primary substrate enters the binding pocket and lastly dioxygen binds to the enzyme-substrate complex. CAS Number: 635-51-8. Take 40mg of the resolved enantiomer and dissolve it in Iml of acetone. Dehydration of succinic acid gives succinic anhydride. [30], In adipocytes, the succinate-activated GPR91 signaling cascade inhibits lipolysis. This application requires Javascript. F. Toda and H. Miyamoto, Chem. 15, 2493 (2015). The enantiomeric excess was 35.5% which is the measurement of purity. The purpose of this experiment is to be able to convert enantiomers of phenylsuccinic acid into separable diastereomers. Filtration permits discard of the more soluble salt, which cames away one enantiomer () of the phenylsuccinic acid Once the less soluble diastereomeric salt has been isolated, only a single enantiomer of phenylsuccinic acid remains. Other information Prepared By Regulatory Affairs Thermo Fisher Scientific Email: EMSDS.RA@thermofisher.com Revision Date 24-Dec-2021 Print Date 24-Dec-2021 Santa Cruz Biotechnology, and the Santa Cruz Biotechnology, Inc. logo, Santa Cruz Animal Health, San Juan Ranch, Supplement of Champions, the San Juan Ranch logo, UltraCruz, ChemCruz, ImmunoCruz, ExactaCruz, and EZ Touch are registered trademarks of Santa Cruz Biotechnology, Inc. All trademarks are the property of their respective owners. A. V. Trask and W. Jones, Top. Jump to main content Jump to site nav. [7] Succinate may thus be produced from enhanced glutamine metabolism via alpha-ketoglutarate or the GABA shunt. [36] Additionally, succinate-promoted activation of HIF-1 generates a pseudo-hypoxic state that can promote tumorneogensis by transcriptional activation of genes involved in proliferation, metabolism and angiogenesis. [32] Arg99, His103, Arg252, and Arg281 near the center of the receptor generate a positively charged binding site for succinate. [7] Activation of inflammatory macrophages through toll-like receptors induces a metabolic shift towards glycolysis. The pathway avoids the decarboxylation steps of the TCA cycle via the enzyme isocitrate lyase which cleaves isocitrate into succinate and glyoxylate. InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14), CSID:86155, http://www.chemspider.com/Chemical-Structure.86155.html (accessed 08:22, Mar 4, 2023), Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, Predicted data is generated using the US Environmental Protection Agencys EPISuite, Click to predict properties on the Chemicalize site, For medical information relating to Covid-19, please consult the. 2) Pre-Lab Report: EXPERIMENTAL SECTION 1) Synthesis of diastereomeric salts: Weigh racemic phenylsuccinic acid (0,5g, 2.57 mmole) and L-prolinc (0.3 g. 2.61 mmole) into a 100 ml boiling flask, and swirl to dissolve the solid. [27] The GABA shunt serves as an alternate route to convert alpha-ketoglutarate into succinate, bypassing the TCA cycle intermediate succinyl-CoA and instead producing the intermediate GABA. Commun. Succinic acid (/sksnk/) is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. [30] Depending on the cell type, GPR91 can interact with multiple G proteins, including Gs, Gi and Gq, and enabling a multitude of signaling outcomes. 4, 339 (2007). [25], Accumulation of fumarate can drive the reverse activity of SDH, thus enhancing succinate generation. Optically active reagents have long been important, in studies of reaction mechanisms because they may offer glimpses at the molecular details of the process, How does one obtain optically active compounds? Finally, succinic semialdehyde is oxidized by succinic semialdehyde dehydrogenase (SSADH) to form succinate, re-entering the TCA cycle and closing the loop. >> Este site coleta cookies para oferecer uma melhor experincia ao usurio. 254, 41 (2005). Two protons are transferred from the phenylsuccinic acid to the proline. out to be a good recrystallization solvent for this product. omeric salt was isolated, the enantiomer of phenylsuccinic acid remains. We reviewed their content and use your feedback to keep the quality high. This work presents more extensive results of separation of phenylsuccinic acid enantiomers by biphasic recognition chiral extraction (BRCE), which is an important intermediate of N-methyl--phensuximide and antitumor agents (in Fig. This involves an acid-base reaction with (s)-proline and restor- To get rid of 2-propanol and any unreacted phenylsuccinic acid, wash the crystals with 10 mL of acetone. Phenylsuccinic acid | C10H10O4 - PubChem Phenylsuccinic acid | C10H10O4 | CID 95459 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. Add 1.15g of finely ground (s)-proline & a magnetic stir bar then mix contents for 2 minutes and reflux for 30 minutes. Insoluble in water. The phenylsuccinic acid is a proton donor making proline the proton acceptor. The only way that these isomers differ physically is the direction in which they rotate plane-polarized light, their optical activity. Vacuum filtered and flushed with 30 mL of acetone: chunky powder, roux-like (S)- With the product collected, specific rotation was calculated where polarimetry is used to calculate the alpha observed in degrees. tract irritation. Chem. Your email subscription to News & Announcements has been received. Cloudiness and then crystals should gradually form.) Article 2) Calculate the enantiomeric excess if the specific rotation obtained after recrystallization is 103.2. 4036-30- (S)-(+)-Phenylsuccinic acid >99 223-719-3 Section 3 - Hazards Identification EMERGENCY OVERVIEW Appearance: almost white solid. solid. [citation needed], Succinate is one of three oncometabolites, metabolic intermediates whose accumulation causes metabolic and non-metabolic dysregulation implicated in tumorigenesis. This property is a direct consequence of the configuration, or orientation of, bonded atoms in space, around the chiral center. Typi- sion of an enantiomer to a di- 24, 861 (1995). indication of why you can't access this Colby College website. Appearance: almost white solid. Determine the mass of purified crystals and prepare a solution to analyze by polarimetry, first measure about 0.4g of your (S)-phenylsuccinic acid and then dissolve in exactly 10mL of HPLC-grade acetone.